US5576460A - Preparation of arylamines - Google Patents
Preparation of arylamines Download PDFInfo
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- US5576460A US5576460A US08/281,449 US28144994A US5576460A US 5576460 A US5576460 A US 5576460A US 28144994 A US28144994 A US 28144994A US 5576460 A US5576460 A US 5576460A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
Definitions
- Migita and coworkers have described the preparation of N,N-diethylaminobenzenes from the palladium-catalyzed reaction of aryl bromides and N,N-diethylaminotributyltin. See, Kosugi et al. Chem. Lett. 1983, 927-928 (1983).
- the general applicability of this synthetic route is limited due to the high reactivity and instability of the aminostannanes (generally, R 3 Sn(NR' 2 )).
- Jones and Lappert report that many aminostannanes are moisture sensitive, decompose or undergo a condensation reaction to form distannazane compounds (generally, (R 3 Sn) 2 NR').
- aminostannanes may hinder their effective isolation and use in subsequent reactions. See, Jones, K. and Lappert, M. F. Organomet. Chem. Rev. 1966 (1), 67-92. Further, the use of aminostannanes is undesirable from an environmental standpoint because of their toxicity.
- Metal amide is meant to include compounds having a metal-amino bond. Such compound also are referred to alternatively as aminometal compounds, such as aminoboranes, aminostannanes, aminosilanes and the like.
- the metal amide may include additional substituents.
- the metal amide has a formula, (Y) m M(NR 1 R 2 ), where Y is selected from the group consisting of alkyl, acyl, aryl, heteroaryl, hydride, alkoxide, thioalkoxide, amides halide and pseudohalide groups and substituted derivatives thereof, and m is selected to satisfy the valency requirement of the metal.
- R 1 and R 2 may be the same or different and are selected from the group consisting of alkyl groups, aromatic groups, cyclic groups such that the free amine is a cyclic amine.
- the aromatic compound has a formula, Ar(Z) n X, where Ar is an aryl moiety, where X is an activated substituent, and where Z is selected from the group consisting of alkyl, aryl, heteroaryl, amino, carboxylic ester, carboxylic acid, acyl, hydrogen, ether, thioether, amide, carboxamide, nitro, phosphonic acid, sulphonic acid, halide, pseudohalide groups, and substituted derivatives thereof, and n is in the range of 0 to 5.
- an arylamine is provided by transaminating a first metal amide, the first metal amide comprising a metal (M) selected from the group consisting of tin, boron, zinc, magnesium, indium and silicon, with a first amine to obtain a second metal amide and a second amine.
- the second metal amide is reacted with an aromatic compound comprising an activated substituent in the presence of a transition metal catalyst to form an arylamine.
- a mixture of arylamines for the screening of pharmaceutical activity is provided by reacting a first metal amide, the metal amide comprising a metal selected from the group consisting of tin, boron, zinc, magnesium, indium and silicon, and a plurality of amines of different composition in a transamination reaction to form a plurality of metal amides of different composition, and thereafter reacting the plurality of metal amides with an aromatic compound comprising an activated substituent in the presence of a transition metal catalyst to form a plurality of arylamines of different composition.
- poly(aniline) is provided by reacting a first metal amide, the metal amide comprising a metal selected from the group consisting of tin, boron, zinc, magnesium, indium and silicon, with a substituted aniline to obtain a metal anilide, and thereafter reacting the substituted metal anilide with a disubstituted aromatic compound, at least one of the substituents being an activated substitute, in the presence of a transition metal catalyst to obtain a poly(aniline).
- the method of the present invention provides a simple general route to a wide range of arylamines and to a range of useful mixtures and arylamine products.
- the present invention is based upon the discovery that a wide range of metal amides are capable of reacting with aromatic compounds containing an activated substituent to obtain an arylamine. Further, readily available metal amide compounds, in particular, aminostannanes, may be subjected to a transamination reaction to obtain new metal amides which may then be reacted with aromatic compounds having an activated substituent to form arylamines.
- a metal amide 1 is reacted with an aromatic compound 2 having an activated substituent, X, in the presence of a catalytic amount of transition metal catalyst.
- the transition metal-catalyzed aromatic amination reaction of eq. 1 most likely proceeds via an initial metal amide-induced reduction of the transition metal catalyst to a zero-valent state, if necessary, followed by an oxidative-addition reaction of the aromatic compound 2 with the metal(0) catalyst, transmetallation and reductive-elimination typical of this class of transition metal catalysts.
- Metal amides suitable for use in the present invention include, by way of example only, amides of tin (also known as aminostannanes), boron (also known as aminoboranes), zinc, magnesium, indium and silicon. It is within the scope of the invention for the metal amide to include additional substituents.
- the metal amide may have the general formula, (Y) m M(NR 1 R 2 ), where the N-substituents, R 1 and R 2 , may be the same or different.
- Suitable R 1 and R 2 include, by way of example only, hydrogen groups, alkyl groups, acyl groups, aromatic and heteroaromatic groups, such substituted phenyl and benzyl and the like, cyclic groups such that the free amine is a cyclic amine, such as piperidine, pyrrolidine and 1,2,3,4-tetrahydroquinoline and the like, and substituted derivatives thereof.
- the metal amide 1 may include additional substituents, Y.
- Y may include alkyl, aryl, acyl, heteroaryl, hydride, alkoxide, thioalkoxide, amide, halide, pseudohalide groups, and substituted derivatives thereof, where m is selected to satisfy the valency requirements of the metal.
- substituted derivatives as that term is used herein, it is meant to include those moieties which have been modified by the addition of substituents that do not significantly affect the properties of that moiety.
- Aromatic compound 2 includes compounds derived from simple aromatic rings, heteroaromatic rings, such as pyridine, quinoline, furan, pyrrole, thiophene, and the like, and fused ring systems, such as naphthalene, anthracene, tetralin, imidizole, indole and the like.
- Suitable aromatic compounds 2 may have the formula (Z) n ArX, where X is an activated substituent.
- An activated substituent, X is characterized as being a good leaving group which readily lends itself to substitution.
- an activated substituent is that moiety whose conjugate acid, HX, has a pKa of less than 5.0.
- Z is an optional substituent on the aromatic ring.
- suitable Z include alkyl, aryl, acyl, heteroaryl, amino, carboxylic ester, carboxylic acid, hydrogen group, ether, thioether, amide, carboxamide, nitro, phosphonic acid, sulphonic acid, halide, pseudohalide groups, and substituted derivatives thereof, and n is in the range of 0 to 5. For fused rings, where the number of substitution sites on the aromatic ring increases, n may be adjusted appropriately.
- a base such as K 2 CO 3 , Tl 2 CO 3 , CsCO 3 , K(t-BuO), Na(t-BuO), K(OPh), Na(OPh) or mixtures thereof. It is particularly advantageous to include one of K(t-BuO), Na(t-BuO), K(OPh) or Na(OPh) with an additional base, preferably K 2 CO 3 , in reactions using boron amide compounds. In other instances, it may be advantageous to include a quaternary ammonium or silver salts.
- N-substituted arylamines may be prepared from any available amine.
- the reaction can be accomplished using a wide range of metal amides, which are either commercially available or obtainable from conventional syntheses using a variety of methods known in the art, such as transamination of metal amides or reaction of the lithium amide with the appropriate metal halide.
- Interested readers additionally are directed to Niedenzu, K and Dawsen, J. W. "Chemistry of Boron and Its Compounds", E. L. Muetterties, Ed.: J. Wiley & Sons, New York, N.Y., 1967, pp 377-442, which is incorporated herein by reference.
- those metal amides which are not readily available or easily isolated may be made by reaction of an activated aromatic compound with a metal amide generated in situ from the reaction of an first metal amide (prepared according to conventional methods) with a second amine. While particularly advantageous when used with aminostannanes because of their difficulty of preparation and isolation using more conventional routes, the method may be used with any of the metal amide compounds of the present invention.
- the starting metal amide 4 may be prepared by any conventional means, typically by reaction of a lithium amide with the appropriate metal halide.
- the starting metal amide 4 is reacted with a second amine 5 in a transamination reaction.
- Metal amide 4 reacts with amine 5 to obtain the metal amide 1 with the concomitant formation of amine 6.
- Transamination is used herein in the conventional sense to mean a reaction in which the amino moieties of two compounds of interest are exchanged, so as to form new species containing the exchanged amino groups.
- Metal amides 4 suitable for use in the present invention include, by way of example only, amides of tin, boron, zinc, magnesium, indium and silicon.
- the conventionally prepared amino compounds may include N-substituents, R 3 and R 4 , which may be the same or different.
- Suitable R 3 and R 4 include, by way of example only, small chain linear alkyl groups.
- the metal amide 4 may include additional substituents, Y.
- Y may include alkyl, aryl, hydride, alkoxide, thioalkoxide, amide, halide, pseudohalide groups, and substituted derivatives thereof, where m is selected to satisfy the valency requirements of the metal.
- Preferred metal amides 4 include, n-Bu 3 SnN(Et) 2 , (Et 2 N) 3 B, (Et 2 N) 2 Zn, (Et 2 N) 2 Mg, (Et 2 N) 3 In and (Et 2 N) 4 Si and comparable NMe 2 derivatives thereof.
- the amine 5 used in the transamination reaction may be any primary or secondary amine or ammonia.
- Suitable amines include aliphatic amines, aromatic amines, cyclic amines and acyclic amines and substituted derivatives thereof.
- the N-substituents, R 1 and R 2 may be the same or different.
- Suitable R 1 and R 2 include, by way of example only, alkyl groups, acyl groups, aromatic and heteroaromatic groups, such substituted phenyl and benzyl and the like, cyclic groups such that the free amine is a cyclic amine, such as piperidine, pyrrolidine and 1,2,3,4-tetrahydroquinoline and the like, and substituted derivatives thereof.
- Suitable as a first amine may be related compounds such as primary and secondary carboxamides, phosphonamides and substituted derivatives thereof.
- the amine 5 is less volatile than the reaction-generated amine 6, thereby facilitating the removal of amine 6 by purging with an inert gas or by reacting under dynamic vacuum. In this way a large number of metal amides may be prepared.
- the transamination reaction and the formation of the arylamine are carried out in the same reaction vessel.
- the metal amide 1 is generated in situ by transamination of metal amide 4 and amine 5 and then is reacted with the aromatic compound 2 in the presence of a catalytic amount of transition metal catalyst. In this way a wide range of N-substituted arylamines 3 may be prepared.
- the transamination reactions and the aromatic amination reactions take place under mild reaction conditions. Reaction can occur at a temperature in the range of room temperature to 200° C., preferably less than 120° C.
- the reactions using metal amides will typically use a near stoichiometric amount of metal amide. However, the reaction may advantageously be accomplished with a catalytic amount of metal amide. In such instances, an amine and an aromatic compound having an activated substituent, X, are reacted in the presence of a catalytic amount of both a metal amide and a transition metal catalyst. The reaction most likely proceeds by the generation of a metal amide from amine, followed by transition metal catalyzed aromatic amination of the aromatic compound to obtain an arylamine. Generation of the arylamine regenerates an active form of the metal to form another metal amide.
- arylamines may be obtained without the use of any metal amides.
- the general reaction is set forth in eq. 3 and is carried out in the presence of a base, such as potassium or sodium carbonate, triethylamine and the like. ##STR3##
- an amide 7 is reacted with an aromatic compound 8 having an activated substituent, X, to form an arylamine 9 in the presence of a catalytic amount of a transition metal catalyst and a base.
- suitable bases include potassium or sodium carbonate and triethylamine and mixtures thereof.
- the reaction requires only catalytic amounts of transition metal catalyst.
- the aromatic compound 8 and the amine 7 may include any of the moieties listed hereinabove for R 1 and R 2 , Z and X.
- the aromatic compound 8 and the amine 7 are included as moieties of a single molecule, whereby the aromatic amination proceeds as an intramolecular process.
- Suitable transition metal catalysts for any of the transition metal catalyzed reactions of the present invention include complexes of platinum, palladium, iron, nickel, ruthenium and rhodium.
- Catalyst complexes may include chelating ligands, such as by way of example only, alkyl and aryl derivatives of phosphines and bisphosphines, imines, arsines, and hybrids thereof, including hybrids of phosphines with amines.
- heterogeneous catalysts containing forms of these elements are also suitable catalysts for any of the transition metal catalyzed reactions of the present invention.
- Catalysts containing palladium and nickel are preferred. It is expected that these catalysts will perform comparably because they are known to undergo similar reactions, namely oxidative-addition reactions and reductive-elimination reactions, which are thought to be involved in the formation of the arylamines of the present invention.
- transition metal catalyst of the present invention, as that term is used herein, shall include any transition metal catalyst and/or catalyst precursor as it is introduced into the reaction vessel and which is, if necessary, converted in situ into the active phase, as well as the active form of the catalyst which participates in the reaction.
- the transition metal catalyst is present in the range of 0.001 to 20 mol %, and preferably 1.0 to 2.5 mol %, with respect to the aromatic compound.
- a combinatorial library for the purposes of the present invention is a mixture of chemically related compounds which may be screened together for a desired biological or agrochemical activity.
- the preparation of many related compounds in a single reaction greatly reduces and simplifies the number of screening processes which need to be carried out. Screening for the appropriate biological, pharmaceutical and agrochemical activity is done by conventional methods.
- a combinatorial library for the screening of pharmaceutical or other related activity may be prepared by reacting in a reaction vessel a first metal amide and a plurality of amines of different composition in a transamination reaction to form a plurality of metal amides comprising the amides of different composition, and thereafter reacting the resulting metal amides with an aromatic compound having an activated substituent in the presence of a transition metal catalyst to form a plurality of arylamines.
- a combinatorial library for the screening of pharmaceutical or other related activity may be prepared by reacting in a reaction vessel a metal amide with a plurality of aromatic compounds of different composition, each having an activated substituent, in the presence of a transition metal catalyst to form a plurality of arylamines.
- a combinatorial library for the screening of pharmaceutical or other related activity may be prepared by reacting in a reaction vessel a first metal amide and a plurality of amines of different composition in a transamination reaction to form a plurality of metal amides comprising the amides of different composition, and thereafter reacting the resulting metal amides with a plurality of aromatic compounds of different composition, each having an activated substituent, in the presence of a transition metal catalyst to form a plurality of arylamines.
- compositions of the metal amides, amines and aromatic compounds having an activated substituent are comparable to those listed herein above for metal amides 1 and 4, amine 5 and aromatic compound 2.
- arylamines may be used in the preparation of polyamines, in particular, poly(anilines).
- poly(anilines) in particular, poly(anilines).
- substituted anilines permits the synthesis of poly(aniline) derivatives according to eq. 4. ##STR4##
- a starting amine 1 is reacted with 1,4-diaminobenzene to form the corresponding metal anilide 10.
- the metal anilide 10 may be further reacted (preferably in situ) with a 1,4-disubstituted aromatic compound 11, where the substituent X is an activated substituent as defined herein, to obtain a poly(aniline) 12.
- the aryl groups, Ar and Ar' may be the same or different. Suitable aryl groups for Ar and Ar' include aryl groups, a heteroaryl group or substituted groups thereof.
- the aryl groups may be a substitutional isomer (i.e., para-, meta-, or ortho-substituted).
- substituted poly(anilines) may be obtained by appropriate selection of substituted 1,4-diaminobenzene derivatives for metal amide 10 and/or selection of substituted 1,4-disubstituted aryl derivatives for aromatic compound 11.
- a metal anilide 13 including an activated aryl substituent, X may be used according to the reaction set forth in eq. 5 to obtain poly(anilines). ##STR5##
- a starting amine 1 is reacted with 1-amino,4-X benzene, where the substituent X is an activated substituent as defined herein, to form the corresponding metal anilide 13.
- the metal anilide 13 reacts (preferably in situ) to obtain a poly(aniline) 12. It should be readily apparent that a wide range of substituted poly(anilines) may be obtained by appropriate selection of substituted aminobenzene derivatives for metal amide 13.
- Metal amides suitable for use in the present invention include, by way of example only, amides of tin (also known as aminostannanes), boron (also known as aminoboranes), zinc, magnesium, indium and silicon.
- the metal amide 10 may include additional substituents, Y.
- Y may include alkyl, aryl, hydride, alkoxide, thioalkoxide, amide, halide, pseudohalide groups, and substituted derivatives thereof, where m is selected to satisfy the valency requirements of the metal, as describe herein above.
- the reaction mixture was cooled, diluted with ethyl ether (20 mL) and extracted with 4N HCl solution (2 ⁇ 10 mL).
- the aqueous fraction was cooled to 0° C., made alkaline with 4N NaOH solution (25-30 mL) and extracted with ethyl ether (2 ⁇ 15 mL).
- the organic fraction was dried with MgSO 4 , concentrated in vacuo and subjected to column chromatography on silica gel using hexane:ethyl acetate (10:1, 4:1) to afford the title compound as a light pink oil (310 mg, 84%).
- Examples 2-10 illustrate the versatility of the method the present invention, in which a transamination reaction is used to prepare a variety of metal amides, which are then reacted in an aromatic amination reaction to form the corresponding arylamine.
- the Pd-catalyzed aromatic aminations are fairly general for a variety of in situ generated aminostannanes.
- Aminostannanes were derived from both aliphatic and aromatic amines including aniline by transamination with N,N-diethylaminotributyltin.
- the resultant aminostannanes undergo Pd-catalyzed reactions with the listed aryl bromides substituted with either electron-withdrawing or electron-donating substituents to afford the desired arylamine in good yields.
- aromatic bromides substituted with a para electron donating group substituent reacted slower than those with a para electron withdrawing group (18 h for 4-bromo-N,N-diethylaniline v 1-2 h for ethyl-4-bromobenzoate).
- Slower reactions were also observed in the case of aminostannanes derived from aniline (30-40 h).
- para-methoxyaniline and N-methylaniline reacted significantly faster (12 h and 8 h, respectively).
- This example illustrates the use of iodide-substituted aromatic compounds.
- This example illustrates the preparation of arylamines from aminoboranes using a homogeneous palladium catalyst with sodium and potassium butoxide and potassium carbonate.
- This example illustrates the preparation of arylamines from aminoboranes using a heterogeneous palladium catalyst in the presence of phosphine ligand and with potassium or sodium butoxide.
- This example illustrates the preparation of arylamines from aminoboranes using a heterogeneous palladium catalyst in the absence of phosphine ligand and with potassium or sodium butoxide and demonstrates that complexing ligands are not necessary for the formation of the active catalytic form.
- This example illustrates the preparation of arylamines without the use of a metal amide.
- the combined organic layers were then stirred with 30% hydrogen peroxide (10 mL) for 20 min at room temperature to oxidize the triphenylphosphine.
- the peroxide layer was separated and the organic layer was washed with water (10 mL).
- the combined water and peroxide layers were then extracted with ethyl ether (2 ⁇ 20 mL).
- the combined organic layers were washed successively with saturated aqueous ferrous sulfate and water (10 mL each).
- the combined ferrous sulfate and water layers were extracted with ethyl ether (2 ⁇ 20 mL).
- the combined organic layers were washed with saturated sodium chloride and dried over anhydrous magnesium sulfate.
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Abstract
Description
TABLE 1 __________________________________________________________________________ ##STR6## No. R" = Amine Work-up.sup.a Aryl Amine Yield __________________________________________________________________________ (%) 2 p-CO.sub.2 Et ##STR7## B ##STR8## 88 3 p-NMe.sub.2 ##STR9## A ##STR10## 81 4 m-Me ##STR11## B ##STR12## 79 5 p-Me ##STR13## A ##STR14## 55 6 m-OMe ##STR15## A ##STR16## 79 7 m-Me ##STR17## B ##STR18## 66 8 m-Me ##STR19## B ##STR20## 64 9 p-Me ##STR21## B ##STR22## 73 10 p-CO.sub.2 Et ##STR23## B ##STR24## 83 __________________________________________________________________________ .sup.a Work-up A: the product was extracted with 4N HCl, followed by neutralization of the aqueous fraction with 4N NaOH and extraction with ethyl ether; workup B: the organics were washed with aqueous KF solution to remove the organostannane as an insoluble nBu.sub.3 SnF polymer.
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US7696210B2 (en) | 2004-06-17 | 2010-04-13 | Wyeth | Gonadotropin releasing hormone receptor antagonists |
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WO2010094285A1 (en) | 2009-02-17 | 2010-08-26 | H. Lundbeck A/S | Purification of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine |
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CN101850270A (en) * | 2010-05-17 | 2010-10-06 | 郑州泰基鸿诺药物科技有限公司 | Application of central palladium phosphine ferrocenylimine complex for catalyzing and synthesizing amine-methylated aromatic compound |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5233090A (en) * | 1988-11-11 | 1993-08-03 | Ricoh Company, Ltd. | [2,2]paracyclophane compounds for use in electrophotographic photoconductors |
US5319009A (en) * | 1992-05-27 | 1994-06-07 | Shell Oil Company | Polymer compositions |
US5382692A (en) * | 1989-03-29 | 1995-01-17 | Ricoh Company, Ltd. | Electrophotographic photoconductors and tertiary amine compounds having condensed polycyclic group for use in the same |
US5403950A (en) * | 1991-03-01 | 1995-04-04 | Ricoh Company, Ltd. | Dipyrenylamine derivatives useful in electrophotographic photoconductors |
-
1994
- 1994-07-27 US US08/281,449 patent/US5576460A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5233090A (en) * | 1988-11-11 | 1993-08-03 | Ricoh Company, Ltd. | [2,2]paracyclophane compounds for use in electrophotographic photoconductors |
US5382692A (en) * | 1989-03-29 | 1995-01-17 | Ricoh Company, Ltd. | Electrophotographic photoconductors and tertiary amine compounds having condensed polycyclic group for use in the same |
US5403950A (en) * | 1991-03-01 | 1995-04-04 | Ricoh Company, Ltd. | Dipyrenylamine derivatives useful in electrophotographic photoconductors |
US5319009A (en) * | 1992-05-27 | 1994-06-07 | Shell Oil Company | Polymer compositions |
Non-Patent Citations (22)
Title |
---|
"Amido-derivatives of Metals and Metalloids. Part IX. Reactions of Tin(IV) and Titanium (IV) Amides with Compounds having Carbonyl and Sulphinyl Multiple Bonds" Chandra et al. J. Chem. Soc. (C) 1969, 2565-8 (1969). |
"Amino-derivatives of Metals and Metalloids. Part I. Preparation of Aminostannanes, Stannylamines, and Stannazanes" Jones, K. and Lappert, M. F. Journal of the Chemical Society 1965 1944-1951 (1965). |
"Aromatic Substitution by the SRN 1 Mechanism" Bunnett, J. F. Accounts of Chemical Research 11, 413-420 (1978). |
"Catalytic and Stoichiometric Metal-Mediated C-N Bond-Forming Processes" Hartwig et al. Paper #235 at the 207th Meeting of the American Chemical Society, Mar. 13-17, 1994, San Diego, California (Abstract only). |
"Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Aza Dienes. Studies on the Total Synthesis of Lavendamycin: Investigative Studies on the Preparation of the CDE β-Carboline Ring System and AB Quinoline-5, 8-quinone Ring System" Boger et al. J. Org. Chem. 50, 5782-5789 (1985). |
"Mechanism and Models for Copper Mediated Nucleophilic Aromatic Substitution. 2. A Single Catalytic Species from Three Different Oxidation States of Copper in an Ullmann Synthesis of Triarylamines" Paine, A. J. J. Chem Soc. 109, 1496-1502 (1987). |
"Nucleophilic Aromatic Substitution Reactions of 1--Methoxy--2--(diphenylphosphinyl)naphthalene with C--, N--, and O--Nucleophiles: Facile Synthesis of Diphenyl(1-substituted-2--naphythyl)phosphines" Hattori et al. Synthesis 1994 199-202 (Feb. 1994). |
"Organic Tin-Nitrogen Compounds" Jones, K. and Lappert, M. F. Organometallic Chemistry Review 1, 67-92 (1966). |
"Palladium-Catalyzed Aromatic Amination of Aryl Bromides with N,N-Di-Ethylamino-Tributyltin" Kosugi et al. Chemistry Letters 1983 927-928 (1983). |
"Palladium-Catalyzed Formation of Carbon-Nitrogen Bonds. Reaction Intermediates and Catalyst Improvements in the Hetero Cross-Coupling of Aryl Halides and Tin Amides" Paul et al. J. Am. Chem. Soc. 116, 5969-5970 (1994). |
"Studies on nucleophilic substitution reactions with cyclopentadienyliron complexes of some chloroarenes and nitroarenes and syntheses and substituted arenes by demetallation of the substitution products" Abd-El-Aziz et al. Journal of Organometallic Chemistry 348, 95-107 (1988). |
Amido derivatives of Metals and Metalloids. Part IX. Reactions of Tin(IV) and Titanium (IV) Amides with Compounds having Carbonyl and Sulphinyl Multiple Bonds Chandra et al. J. Chem. Soc. (C) 1969, 2565 8 (1969). * |
Amino derivatives of Metals and Metalloids. Part I. Preparation of Aminostannanes, Stannylamines, and Stannazanes Jones, K. and Lappert, M. F. Journal of the Chemical Society 1965 1944 1951 (1965). * |
Aromatic Substitution by the S RN 1 Mechanism Bunnett, J. F. Accounts of Chemical Research 11, 413 420 (1978). * |
Catalytic and Stoichiometric Metal Mediated C N Bond Forming Processes Hartwig et al. Paper 235 at the 207th Meeting of the American Chemical Society, Mar. 13 17, 1994, San Diego, California (Abstract only). * |
Inverse Electron Demand Diels Alder Reactions of Heterocyclic Aza Dienes. Studies on the Total Synthesis of Lavendamycin: Investigative Studies on the Preparation of the CDE Carboline Ring System and AB Quinoline 5, 8 quinone Ring System Boger et al. J. Org. Chem. 50, 5782 5789 (1985). * |
Mechanism and Models for Copper Mediated Nucleophilic Aromatic Substitution. 2. A Single Catalytic Species from Three Different Oxidation States of Copper in an Ullmann Synthesis of Triarylamines Paine, A. J. J. Chem Soc. 109, 1496 1502 (1987). * |
Nucleophilic Aromatic Substitution Reactions of 1 Methoxy 2 (diphenylphosphinyl)naphthalene with C , N , and O Nucleophiles: Facile Synthesis of Diphenyl(1 substituted 2 naphythyl)phosphines Hattori et al. Synthesis 1994 199 202 (Feb. 1994). * |
Organic Tin Nitrogen Compounds Jones, K. and Lappert, M. F. Organometallic Chemistry Review 1, 67 92 (1966). * |
Palladium Catalyzed Aromatic Amination of Aryl Bromides with N,N Di Ethylamino Tributyltin Kosugi et al. Chemistry Letters 1983 927 928 (1983). * |
Palladium Catalyzed Formation of Carbon Nitrogen Bonds. Reaction Intermediates and Catalyst Improvements in the Hetero Cross Coupling of Aryl Halides and Tin Amides Paul et al. J. Am. Chem. Soc. 116, 5969 5970 (1994). * |
Studies on nucleophilic substitution reactions with cyclopentadienyliron complexes of some chloroarenes and nitroarenes and syntheses and substituted arenes by demetallation of the substitution products Abd El Aziz et al. Journal of Organometallic Chemistry 348, 95 107 (1988). * |
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US20060099687A1 (en) * | 1998-09-02 | 2006-05-11 | Glucksmann Maria A | 14926 Receptor, a novel G-protein coupled receptor |
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US6855839B2 (en) | 1999-05-17 | 2005-02-15 | Univation Technologies, Llc, (Us) | Method of polymerization |
US6235938B1 (en) | 1999-06-10 | 2001-05-22 | Yale University | Transition metal-catalyzed process for preparing N-aryl amine compounds |
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US7582636B2 (en) | 2005-05-26 | 2009-09-01 | Wyeth | Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of Gonadotropin Releasing Hormone receptor |
US20090234126A1 (en) * | 2006-03-21 | 2009-09-17 | Yale University | Process for the Synthesis of Arylamines from the Reaction of an Aromatic Compound with Ammonia or a Metal Amide |
US8058477B2 (en) | 2006-03-21 | 2011-11-15 | Yale University | Process for the synthesis of arylamines from the reaction of an aromatic compound with ammonia or a metal amide |
WO2007109365A2 (en) | 2006-03-21 | 2007-09-27 | Yale University | Process for the synthesis of arylamines from the reaction of an aromatic compound with ammonia or a metal amide |
US8084611B2 (en) | 2006-03-30 | 2011-12-27 | Mitsubishi Tanabe Pharma Corporation | Process for preparing tetrahydroquinoline derivatives |
US8093409B2 (en) * | 2006-08-22 | 2012-01-10 | Nippon Shokubai Co., Ltd. | Method for producing cyclic unsaturated compound |
US20090299009A1 (en) * | 2006-08-22 | 2009-12-03 | Nippon Shokubai Co., Ltd. | Method for producing cyclic unsaturated compound |
US11407751B2 (en) | 2007-03-12 | 2022-08-09 | Intra-Cellular Therapies, Inc. | Hydrochloric acid salt of (6bR,10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline |
US10597395B2 (en) | 2007-03-12 | 2020-03-24 | Intra-Cellular Therapies, Inc. | Preparation of certain substituted 1-(4-fluorophenyl)-4-(2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-YL)butan-1-ones and pharmaceutically acceptable salts thereof |
US10221176B2 (en) | 2007-03-12 | 2019-03-05 | Intra-Cellular Therapies, Inc. | Preparation of certain substituted [((6bR,10aS)-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalines and pharmaceutically acceptable salts thereof |
US20100113781A1 (en) * | 2007-03-12 | 2010-05-06 | Intracellular Therapies, Inc. | Substituted heterocycle gamma-carbolines synthesis |
US8779139B2 (en) | 2007-03-12 | 2014-07-15 | Intra-Cellular Therapies, Inc. | Substituted 2,3,4,4A,5,9B-hexahydro-1H-pyrido[4,3-B]indole derivatives synthesis and uses thereof |
US8309722B2 (en) | 2007-03-12 | 2012-11-13 | Intra-Cellular Therapies, Inc. | Substituted heterocycle gamma-carbolines synthesis |
US11066407B2 (en) | 2007-03-12 | 2021-07-20 | Intra-Cellular Therapies, Inc. | Preparation of certain substituted 1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalines and pharmaceutically acceptable salts thereof |
US10464938B2 (en) | 2007-03-12 | 2019-11-05 | Intra-Cellular Therapies, Inc. | Pharmaceutical compositions comprising ((6bR,10aS)-1-(4-fluorophenyl)-4-(3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)butan-1-one or pharmaceutically acceptable salts thereof |
US9751883B2 (en) | 2007-03-12 | 2017-09-05 | Intra-Cellular Therapies, Inc. | Preparation of certain [((6BR,10AS)-2,3,6B,7,8,9,10, 10A-octahydro-1H-pyrido[3′,4′:4,5]pyrrolo [1,2,3-de]quinoxalines and pharmaceutically acceptable salts thereof |
US9315504B2 (en) | 2007-03-12 | 2016-04-19 | Intra-Cellular Therapies, Inc. | Preparation of 4-((6BR,10AS)-3-methyl-2,3,6B,9,10, 10A-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo [1,2,3-de]quinoxalin-8-(7H)-yl)-1-(4-fluorophenyl)-1-butanone or a pharmaceutically acceptable salt thereof |
EP2163544A1 (en) | 2008-09-16 | 2010-03-17 | Pfizer, Inc. | Methods of preparing indazole compounds |
US20110207599A1 (en) * | 2008-11-10 | 2011-08-25 | Univation Technologies, Llc | Processes for the Preparation of Arylamine Compounds |
US8501659B2 (en) | 2008-11-10 | 2013-08-06 | Univation Technologies, Llc | Processes for the preparation of arylamine compounds |
WO2010094285A1 (en) | 2009-02-17 | 2010-08-26 | H. Lundbeck A/S | Purification of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine |
JP2010260815A (en) * | 2009-05-07 | 2010-11-18 | Konica Minolta Holdings Inc | Method for producing nitrogen-containing condensed heterocyclic compound |
US8633316B2 (en) | 2010-01-25 | 2014-01-21 | Konica Minolta Holdings, Inc. | Producing method of nitrogen containing condensed heterocyclic compound |
US20110184176A1 (en) * | 2010-01-25 | 2011-07-28 | Konica Minolta Holdings, Inc. | Producing method of nitrogen containing condensed heterocyclic compound |
CN101850270A (en) * | 2010-05-17 | 2010-10-06 | 郑州泰基鸿诺药物科技有限公司 | Application of central palladium phosphine ferrocenylimine complex for catalyzing and synthesizing amine-methylated aromatic compound |
CN103917522B (en) * | 2011-09-02 | 2016-06-15 | 高砂香料工业株式会社 | The manufacture method of N-(assorted) arylazoles |
AU2012302599B2 (en) * | 2011-09-02 | 2016-09-01 | Takasago International Corporation | Process for producing N-(hetero)arylazoles |
CN103917522A (en) * | 2011-09-02 | 2014-07-09 | 高砂香料工业株式会社 | Process for producing n-(hetero)arylazoles |
WO2013032035A1 (en) | 2011-09-02 | 2013-03-07 | Takasago International Corporation | Process for producing n-(hetero)arylazoles |
KR20140057272A (en) | 2011-09-02 | 2014-05-12 | 다카사고 고료 고교 가부시키가이샤 | Process for producing n-(hetero)arylazoles |
US9233922B2 (en) * | 2011-09-02 | 2016-01-12 | Takasago International Corporation | Process for producing N-(hetero)arylazoles |
US20140371461A1 (en) * | 2011-09-02 | 2014-12-18 | Takasago International Corporation | Process for producing n-(hetero)arylazoles |
US9499474B2 (en) | 2011-11-11 | 2016-11-22 | Merck Patent Gmbh | Process for producing arylamines |
WO2013068075A1 (en) | 2011-11-11 | 2013-05-16 | Merck Patent Gmbh | Process for producing arylamines |
US11958852B2 (en) | 2012-04-14 | 2024-04-16 | Intra-Cellular Therapies, Inc. | Compounds and methods |
US11124514B2 (en) | 2012-04-14 | 2021-09-21 | Intra-Cellular Therapies, Inc. | Compositions and methods |
US11053245B2 (en) | 2012-04-14 | 2021-07-06 | Intra-Cellular Therapies, Inc. | Methods |
US9707551B2 (en) | 2013-01-23 | 2017-07-18 | Hokko Chemical Industry Co., Ltd. | Reaction catalyst for cross-coupling and method for manufacturing aromatic compound |
US9956227B2 (en) | 2013-12-03 | 2018-05-01 | Intra-Cellular Therapies, Inc. | Method for the treatment of residual symptoms of schizophrenia |
US10322134B2 (en) | 2013-12-03 | 2019-06-18 | Intra-Cellular Therapies, Inc. | Methods |
US10960009B2 (en) | 2013-12-03 | 2021-03-30 | Intra-Cellular Therapies, Inc. | Methods of treating schizophrenia and depression |
US9745300B2 (en) | 2014-04-04 | 2017-08-29 | Intra-Cellular Therapies, Inc. | Organic compounds |
US11560382B2 (en) | 2014-04-04 | 2023-01-24 | Intra-Cellular Therapies, Inc. | Organic compounds |
US10077267B2 (en) | 2014-04-04 | 2018-09-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
US10899762B2 (en) | 2014-04-04 | 2021-01-26 | Intra-Cellular Therapies, Inc. | Organic compounds |
US10597394B2 (en) | 2014-04-04 | 2020-03-24 | Intra-Cellular Therapies, Inc. | Organic compounds |
US11844757B2 (en) | 2016-01-26 | 2023-12-19 | Intra-Cellular Therapies, Inc. | Organic compounds |
US10799500B2 (en) | 2016-01-26 | 2020-10-13 | Intra-Cellular Therapies, Inc. | Organic compounds |
US10245260B2 (en) | 2016-01-26 | 2019-04-02 | Intra-Cellular Therapies, Inc. | Organic compounds |
US11096944B2 (en) | 2016-03-25 | 2021-08-24 | Intra-Cellular Therapies, Inc. | Organic compounds |
US10688097B2 (en) | 2016-03-25 | 2020-06-23 | Intra-Cellular Therapies, Inc. | Organic compounds |
US11014925B2 (en) | 2016-03-28 | 2021-05-25 | Intra-Cellular Therapies, Inc. | Co-crystals of 1-(4-fluoro-phenyl)-4-((6bR,1OaS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H,7H- pyrido[3′,4′:4,51_pyrrolo [1,2,3-delqcuinoxalin-8-yl)-butan-1-one with nicotinamide or isonicotinamide |
US10654854B2 (en) | 2016-03-28 | 2020-05-19 | Intra-Cellular Therapies, Inc. | Salts and crystals of ITI-007 |
US10682354B2 (en) | 2016-03-28 | 2020-06-16 | Intra-Cellular Therapies, Inc. | Compositions and methods |
US11331316B2 (en) | 2016-10-12 | 2022-05-17 | Intra-Cellular Therapies, Inc. | Amorphous solid dispersions |
US11311536B2 (en) | 2016-10-12 | 2022-04-26 | Intra-Cellular Therapies, Inc. | Amorphous solid dispersions |
US11826367B2 (en) | 2016-10-12 | 2023-11-28 | Intra-Cellular Therapies, Inc. | Amorphous solid dispersions |
US11872223B2 (en) | 2016-10-12 | 2024-01-16 | Intra-Cellular Therapies, Inc. | Amorphous solid dispersions |
US10906906B2 (en) | 2016-12-29 | 2021-02-02 | Intra-Cellular Therapies, Inc. | Organic compounds |
US10961245B2 (en) | 2016-12-29 | 2021-03-30 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines for treatment of central nervous system disorders |
US10716786B2 (en) | 2017-03-24 | 2020-07-21 | Intra-Cellular Therapies, Inc. | Transmucosal and subcutaneous compositions |
US11052083B2 (en) | 2017-03-24 | 2021-07-06 | Intra-Cellular Therapies, Inc. | Transmucosal methods for treating psychiatric and neurological conditions |
US11806347B2 (en) | 2017-03-24 | 2023-11-07 | Intra-Cellular Therapies, Inc. | Transmucosal methods for treating psychiatric and neurological conditions |
US11376249B2 (en) | 2017-07-26 | 2022-07-05 | Intra-Cellular Therapies, Inc. | Organic compounds |
US11427587B2 (en) | 2017-07-26 | 2022-08-30 | Intra-Cellular Therapies, Inc. | Organic compounds |
US11773095B2 (en) | 2017-07-26 | 2023-10-03 | Intra-Cellular Therapies, Inc. | Organic compounds |
KR20200118215A (en) | 2018-03-02 | 2020-10-14 | 타나카 세이미츠 코교 가부시키가이샤 | Adhesive application device and adhesive application method |
US12023331B2 (en) | 2018-06-08 | 2024-07-02 | Intra-Cellular Therapies, Inc. | Methods |
US11453670B2 (en) | 2018-06-11 | 2022-09-27 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines synthesis |
WO2020007770A1 (en) | 2018-07-04 | 2020-01-09 | Merck Patent Gmbh | Process for the production of arylamines |
US11806348B2 (en) | 2018-08-31 | 2023-11-07 | Intra-Cellular Therapies, Inc. | Methods of treatment using pharmaceutical capsule compositions comprising lumateperone mono-tosylate |
US11052084B2 (en) | 2018-08-31 | 2021-07-06 | Intra-Cellular Therapies, Inc. | Pharmaceutical capsule compositions comprising lumateperone mono-tosylate |
US11957791B2 (en) | 2018-08-31 | 2024-04-16 | Intra-Cellular Therapies, Inc. | Methods |
US12070459B2 (en) | 2018-08-31 | 2024-08-27 | Intra-Cellular Therapies, Inc. | Pharmaceutical capsule compositions comprising lumateperone mono-tosylate |
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